Questions to Ask Billionaires

The questions

Open any question to see why it works.

1. 1

   What were you doing for money before the thing that worked?

   The job just before the success is usually left out of the retelling, and it is the most human part of the story. It also dates the moment things turned, which lets you ask about the year rather than the legend.

2. 2

   What was the decision that made the difference?

   Ask for one. Forcing a single answer gets past the list of contributing factors and usually produces something specific and unglamorous, such as a pricing change or a refusal to sell.

3. 3

   How much of this was timing?

   The honest ones name a market condition, a technology arriving, or a competitor stumbling. Someone who claims none of it was timing is either performing or has never examined the question, and either is worth knowing.

4. 4

   Who told you no, and were they right?

   The second half is the real question. Most successful people collect rejection stories as trophies, and asking whether the rejection was reasonable at the time turns the anecdote into an actual assessment.

5. 5

   What is the largest amount of money you have lost?

   Losses are less rehearsed than wins and reveal how someone thinks about risk now. Follow up on what they changed afterwards, since the answer separates people who learned something from people who got lucky twice.

6. 6

   What do you do when you do not know something?

   Ask about the method: who they call, what they read, how long they sit with it. At scale, the process for handling ignorance matters more than what any one person knows, and few people are ever asked to describe theirs.

7. 7

   How do you find out when something is going wrong?

   Bad news travels slowly upward and everyone in this position knows it. What they have built to counteract it, skip-level meetings, unfiltered channels, walking the floor, is a concrete answer about how the organisation really runs.

8. 8

   Who is allowed to tell you that you are wrong?

   Ask for names and roles, not a principle. Someone who cannot name anyone specific has answered the question, and someone who names a spouse, an old friend, or a long-serving colleague is describing their real check on themselves.

9. 9

   What do you spend money on that you would defend to anyone?

   This gets past both the humblebrag and the false modesty. The thing someone will defend out loud, whether it is a plane, a chef, or a very good mattress, is a clean statement of what they think money is for.

10. 10

    What has money not fixed?

    Asked plainly, this usually gets a serious answer, because it is the question people at this level actually think about. Health, family, and the loss of ordinary friction come up more often than anything financial.

11. 11

    How did your friendships change?

    Every large change in wealth reorders relationships, and almost nobody asks about it directly. Listen for whether the friends from before are still there and what had to happen for that to be true.

12. 12

    What do you want your children to have to do for themselves?

    The practical version of the inheritance question, and it gets a more thoughtful answer. Where someone draws the line, education, a first home, business capital, is a concrete statement of what they believe about earning.

13. 13

    How do you decide what to give away, and who decides with you?

    Ask about the mechanism rather than the causes. Whether giving is directed personally, run by staff, or delegated to a foundation tells you how much of it is a conviction and how much is an institution.

14. 14

    What do you own now that you no longer enjoy?

    Possessions bought at a peak often become obligations, and this question invites an unusually honest answer about that. It also reliably produces a good story about a boat, a house, or a horse.

15. 15

    What is the first thing you check in the morning?

    Concrete and revealing. The number, message, or dashboard someone reaches for first is what they are actually responsible for, regardless of what their title says.

16. 16

    How do you decide what to say yes to now?

    When money stops being the constraint, attention becomes the constraint, and the filter people build for it is genuinely interesting. Ask what their rule is and what the last thing they said no to was.

17. 17

    What would have to happen for you to lose all of this?

    Most people at this level have a specific fear rather than a vague one: a regulatory change, a concentrated holding, a lawsuit, a health event. Naming it tells you where they think they are fragile.

18. 18

    What do people always ask you that you find tiresome?

    Asking it directly buys goodwill and steers the rest of the conversation off the worn track. It also tells you what the public story about them is, seen from their side of it.

19. 19

    What do you think you were wrong about ten years ago?

    This requires a real answer and cannot be prepared as easily as a lesson learned. If nothing comes to mind after a pause, that is an answer too, and it colours everything else they have said.

20. 20

    What do you want to be doing at eighty?

    It moves the conversation off accumulation and onto what all of it was for. People are usually more candid about this than about anything involving numbers, and it is a good place to finish.